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Passerini Reaction
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This reaction is an atom‐economical 3‐component condensation among isonitrile (i.e., isocyanide), carboxylic acid, and aldehyde (or ketone) to form α‐acyloxy amide through acyl rearrangement and tautomerization and is generally known as the Passerini reaction.
This reaction has been modified to occur in aqueous solution with obvious advantages of a high reaction rate and easy separation. Lewis acid and Lewis base have been used to promote the Passerini reaction. This reaction has wide applications in combinatorial synthesis.
Of the 3 components, the carbonyl group is one of the most critical reactants because of the pronounced reactivity of the divalent isonitrile carbon atom towards the C(sp2) electrophilic center.
This reaction can be sluggish with low yields if a strong carboxylic acid or an unusually electrophilic carbonyl compound is not used.
The traditional Passerini reaction involves an aldehyde in the one pot reaction. In some cases, the aldehydes are not stable or are difficult to handle. Ngouansavanh et al. recently describes substituting the aldehyde with the corresponding alcohol and using 2-Iodoxybenzoic acid (IBX). This increases the versatility and the number of compounds available using this reaction scheme.
This reaction has been modified to occur in aqueous solution with obvious advantages of a high reaction rate and easy separation. Lewis acid and Lewis base have been used to promote the Passerini reaction. This reaction has wide applications in combinatorial synthesis.
Of the 3 components, the carbonyl group is one of the most critical reactants because of the pronounced reactivity of the divalent isonitrile carbon atom towards the C(sp2) electrophilic center.
This reaction can be sluggish with low yields if a strong carboxylic acid or an unusually electrophilic carbonyl compound is not used.
The traditional Passerini reaction involves an aldehyde in the one pot reaction. In some cases, the aldehydes are not stable or are difficult to handle. Ngouansavanh et al. recently describes substituting the aldehyde with the corresponding alcohol and using 2-Iodoxybenzoic acid (IBX). This increases the versatility and the number of compounds available using this reaction scheme.
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